Identification
NameVarenicline
Accession NumberDB01273
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionVarenicline is a prescription medication used to treat smoking addiction. This medication is the first approved nicotinic receptor partial agonist. Specifically, varenicline is a partial agonist of the alpha4/beta2 subtype of the nicotinic acetylcholine receptor. In addition it acts on alpha3/beta4 and weakly on alpha3beta2 and alpha6-containing receptors. A full agonism was displayed on alpha7-receptors. On March 9, 2015, the U.S. Food and Drug Administration warned that Varenicline, in the form of Pfizer Inc's quit-smoking drug, Chantix, has been associated with seizures and that some patients who drink while taking the drug may become aggressive or black out. Pfizer is conducting an additional safety study of the drug, results of which are expected in late 2015. The FDA said it is keeping the black box in place at least until the results of the trial are announced.
Structure
Thumb
Synonyms
CP-526,555
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Varenicline tartrate82269ASB48 375815-87-5TWYFGYXQSYOKLK-LREBCSMRSA-NDetails
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ChampixTablet, film coated1 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated1.0 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated1.0 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet0.5 mgOralPfizer2007-04-11Not applicableCanada
ChampixTablet, film coated1 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated1 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated0.5 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet1.0 mgOralPfizer2007-04-11Not applicableCanada
ChampixTablet, film coated1 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated1 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated0.5 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated0.5 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated1 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated1.0 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated0.5 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated1 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated1.0 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated0.5 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated1.0 mgOralPfizer2006-09-26Not applicableEu
ChampixTablet, film coated1.0 mgOralPfizer2006-09-26Not applicableEu
ChantixKitA S Medication Solutions2006-05-10Not applicableUs
ChantixTablet, film coated.5 mg/1OralRebel Distributors2006-05-10Not applicableUs
ChantixKitLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2006-05-10Not applicableUs
ChantixTablet, film coated.5 mg/1OralAvera Mc Kennan Hospital2016-01-22Not applicableUs
ChantixKitRebel Distributors2006-05-10Not applicableUs
ChantixKitPhysicians Total Care, Inc.2006-09-01Not applicableUs
ChantixTablet, film coated.5 mg/1OralPfizer Laboratories Div Pfizer Inc.2006-05-10Not applicableUs
ChantixTablet, film coated1 mg/1OralRebel Distributors2006-05-10Not applicableUs
ChantixTablet, film coated1 mg/1OralPhysicians Total Care, Inc.2006-09-01Not applicableUs
ChantixTablet, film coated1 mg/1OralPfizer Laboratories Div Pfizer Inc.2006-05-10Not applicableUs
ChantixTablet, film coated.5 mg/1OralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2011-12-282016-12-21Us
ChantixTablet, film coated.5 mg/1OralCardinal Health2006-05-10Not applicableUs
ChantixKitPfizer Laboratories Div Pfizer Inc.2006-05-10Not applicableUs
ChantixTablet, film coated1 mg/1OralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-02-23Not applicableUs
ChantixKitU.S. Pharmaceuticals2006-05-10Not applicableUs
ChantixTablet, film coated.5 mg/1OralCarilion Materials Management2006-05-10Not applicableUs
ChantixTablet, film coated1 mg/1OralA S Medication Solutions2006-05-10Not applicableUs
ChantixTablet, film coated1 mg/1OralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-02-23Not applicableUs
ChantixTablet, film coated1 mg/1OralCarilion Materials Management2006-05-10Not applicableUs
ChantixKitProficient Rx LP2006-05-10Not applicableUs
Gd-vareniclineTablet0.5 mgOralGenmed A Division Of Pfizer Canada IncNot applicableNot applicableCanada
Gd-vareniclineTablet1.0 mgOralGenmed A Division Of Pfizer Canada IncNot applicableNot applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
ChampixPfizer
Gd-vareniclineGenmed A Division Of Pfizer Canada Inc
Categories
UNIIW6HS99O8ZO
CAS number249296-44-4
WeightAverage: 211.2624
Monoisotopic: 211.110947431
Chemical FormulaC13H13N3
InChI KeyJQSHBVHOMNKWFT-DTORHVGOSA-N
InChI
InChI=1S/C13H13N3/c1-2-16-13-5-11-9-3-8(6-14-7-9)10(11)4-12(13)15-1/h1-2,4-5,8-9,14H,3,6-7H2/t8-,9+
IUPAC Name
(1R,12S)-5,8,14-triazatetracyclo[10.3.1.0²,¹¹.0⁴,⁹]hexadeca-2,4,6,8,10-pentaene
SMILES
[H][C@]12C[C@]([H])(CNC1)C1=CC3=NC=CN=C3C=C21
Pharmacology
IndicationFor use as an aid in smoking cessation.
Structured Indications Not Available
PharmacodynamicsVarenicline is a partial nicotinic acetylcholine receptor agonist, designed to partially activate this system while displacing nicotine at its sites of action in the brain.
Mechanism of actionVarenicline is an alpha-4 beta-2 neuronal nicotinic acetylcholine receptor partial agonist. The drug shows high selectiviyty for this receptor subclass, relative to other nicotinic receptors (>500-fold alpha-3 beta-4, >3500-fold alpha-7, >20,000-fold alpha-1 beta gamma delta) or non-nicotinic receptors and transporters (>2000-fold). The drug competitively inhibits the ability of nicotine to bind to and activate the alpha-4 beta-2 receptor. The drug exerts mild agonistic activity at this site, though at a level much lower than nicotine; it is presumed that this activation eases withdrawal symptoms.
TargetKindPharmacological actionActionsOrganismUniProt ID
Neuronal acetylcholine receptor subunit alpha-4Proteinyes
partial agonist
HumanP43681 details
Neuronal acetylcholine receptor subunit alpha-7Proteinunknown
agonist
HumanP36544 details
Neuronal acetylcholine receptor subunit alpha-3Proteinunknown
partial agonist
HumanP32297 details
Neuronal acetylcholine receptor subunit alpha-6Proteinunknown
partial agonist
HumanQ15825 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingLess than 20%.
Metabolism

Metabolism is limited (<10%). Most of the active compound is excreted renally (81%). A small proportion is glucuronidated, oxidated, N-formylated or conjugated to a hexose.

Route of eliminationVarenicline undergoes minimal metabolism, with 92% excreted unchanged in the urine. Renal elimination of varenicline is primarily through glomerular filtration along with active tubular secretion possibly via the organic cation transporter, OCT2.
Half lifeThe elimination half-life of varenicline is approximately 24 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when 1,10-Phenanthroline is combined with Varenicline.Experimental
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Varenicline.Approved
AlprenololThe risk or severity of adverse effects can be increased when Alprenolol is combined with Varenicline.Approved, Withdrawn
AmbenoniumThe risk or severity of adverse effects can be increased when Ambenonium is combined with Varenicline.Approved
ArotinololThe risk or severity of adverse effects can be increased when Arotinolol is combined with Varenicline.Approved
AsenapineThe serum concentration of Varenicline can be increased when it is combined with Asenapine.Approved
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Varenicline.Approved
BefunololThe risk or severity of adverse effects can be increased when Befunolol is combined with Varenicline.Experimental
BetaxololThe risk or severity of adverse effects can be increased when Betaxolol is combined with Varenicline.Approved
BevantololThe risk or severity of adverse effects can be increased when Bevantolol is combined with Varenicline.Approved
BisoprololThe risk or severity of adverse effects can be increased when Bisoprolol is combined with Varenicline.Approved
BopindololThe risk or severity of adverse effects can be increased when Bopindolol is combined with Varenicline.Approved
BufuralolThe risk or severity of adverse effects can be increased when Bufuralol is combined with Varenicline.Experimental, Investigational
BupranololThe risk or severity of adverse effects can be increased when Bupranolol is combined with Varenicline.Approved
CarteololThe risk or severity of adverse effects can be increased when Carteolol is combined with Varenicline.Approved
CarvedilolThe risk or severity of adverse effects can be increased when Carvedilol is combined with Varenicline.Approved, Investigational
CeliprololThe risk or severity of adverse effects can be increased when Celiprolol is combined with Varenicline.Approved, Investigational
CimetidineThe serum concentration of Varenicline can be increased when it is combined with Cimetidine.Approved
CimetropiumVarenicline may decrease the anticholinergic activities of Cimetropium.Experimental
CinoxacinThe serum concentration of Varenicline can be increased when it is combined with Cinoxacin.Approved, Withdrawn
CiprofloxacinThe serum concentration of Varenicline can be increased when it is combined with Ciprofloxacin.Approved, Investigational
DecamethoniumThe risk or severity of adverse effects can be increased when Decamethonium is combined with Varenicline.Approved
DemecariumThe risk or severity of adverse effects can be increased when Demecarium is combined with Varenicline.Approved
DonepezilThe risk or severity of adverse effects can be increased when Donepezil is combined with Varenicline.Approved
DoxepinThe serum concentration of Varenicline can be increased when it is combined with Doxepin.Approved
EchothiophateThe risk or severity of adverse effects can be increased when Echothiophate is combined with Varenicline.Approved
EdrophoniumThe risk or severity of adverse effects can be increased when Edrophonium is combined with Varenicline.Approved
EnoxacinThe serum concentration of Varenicline can be increased when it is combined with Enoxacin.Approved
EpinastineThe serum concentration of Varenicline can be increased when it is combined with Epinastine.Approved, Investigational
EsmololThe risk or severity of adverse effects can be increased when Esmolol is combined with Varenicline.Approved
EthanolThe risk or severity of adverse effects can be increased when Varenicline is combined with Ethanol.Approved
FamotidineThe serum concentration of Varenicline can be increased when it is combined with Famotidine.Approved
FleroxacinThe serum concentration of Varenicline can be increased when it is combined with Fleroxacin.Approved
FlumequineThe serum concentration of Varenicline can be increased when it is combined with Flumequine.Withdrawn
GalantamineThe risk or severity of adverse effects can be increased when Galantamine is combined with Varenicline.Approved
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Gallamine Triethiodide is combined with Varenicline.Approved
GatifloxacinThe serum concentration of Varenicline can be increased when it is combined with Gatifloxacin.Approved, Investigational
GemifloxacinThe serum concentration of Varenicline can be increased when it is combined with Gemifloxacin.Approved, Investigational
Ginkgo bilobaThe risk or severity of adverse effects can be increased when Ginkgo biloba is combined with Varenicline.Approved, Nutraceutical
GrepafloxacinThe serum concentration of Varenicline can be increased when it is combined with Grepafloxacin.Withdrawn
Huperzine AThe risk or severity of adverse effects can be increased when Huperzine A is combined with Varenicline.Investigational
IndenololThe risk or severity of adverse effects can be increased when Indenolol is combined with Varenicline.Withdrawn
IsoflurophateThe risk or severity of adverse effects can be increased when Isoflurophate is combined with Varenicline.Approved, Withdrawn
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Varenicline.Approved
LevobunololThe risk or severity of adverse effects can be increased when Levobunolol is combined with Varenicline.Approved
LevofloxacinThe serum concentration of Varenicline can be increased when it is combined with Levofloxacin.Approved, Investigational
LomefloxacinThe serum concentration of Varenicline can be increased when it is combined with Lomefloxacin.Approved
MalathionThe risk or severity of adverse effects can be increased when Malathion is combined with Varenicline.Approved, Investigational
MefloquineThe risk or severity of adverse effects can be increased when Mefloquine is combined with Varenicline.Approved
MemantineThe risk or severity of adverse effects can be increased when Memantine is combined with Varenicline.Approved, Investigational
MethanthelineThe serum concentration of Varenicline can be increased when it is combined with Methantheline.Approved
MetiamideThe serum concentration of Varenicline can be increased when it is combined with Metiamide.Experimental
MetipranololThe risk or severity of adverse effects can be increased when Metipranolol is combined with Varenicline.Approved
MetoprololThe risk or severity of adverse effects can be increased when Metoprolol is combined with Varenicline.Approved, Investigational
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Varenicline.Approved
MoxifloxacinThe serum concentration of Varenicline can be increased when it is combined with Moxifloxacin.Approved, Investigational
NadololThe risk or severity of adverse effects can be increased when Nadolol is combined with Varenicline.Approved
Nalidixic AcidThe serum concentration of Varenicline can be increased when it is combined with Nalidixic Acid.Approved
NeostigmineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Varenicline.Approved, Vet Approved
NicotineThe risk or severity of adverse effects can be increased when Varenicline is combined with Nicotine.Approved
NizatidineThe serum concentration of Varenicline can be increased when it is combined with Nizatidine.Approved
NorfloxacinThe serum concentration of Varenicline can be increased when it is combined with Norfloxacin.Approved
OfloxacinThe serum concentration of Varenicline can be increased when it is combined with Ofloxacin.Approved
OlanzapineThe serum concentration of Varenicline can be increased when it is combined with Olanzapine.Approved, Investigational
OxprenololThe risk or severity of adverse effects can be increased when Oxprenolol is combined with Varenicline.Approved
PefloxacinThe serum concentration of Varenicline can be increased when it is combined with Pefloxacin.Approved
PenbutololThe risk or severity of adverse effects can be increased when Penbutolol is combined with Varenicline.Approved, Investigational
PhysostigmineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Varenicline.Approved
PindololThe risk or severity of adverse effects can be increased when Pindolol is combined with Varenicline.Approved
PractololThe risk or severity of adverse effects can be increased when Practolol is combined with Varenicline.Approved
PropranololThe risk or severity of adverse effects can be increased when Propranolol is combined with Varenicline.Approved, Investigational
PyridostigmineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Varenicline.Approved
RanitidineThe serum concentration of Varenicline can be increased when it is combined with Ranitidine.Approved
RivastigmineThe risk or severity of adverse effects can be increased when Rivastigmine is combined with Varenicline.Approved, Investigational
RosoxacinThe serum concentration of Varenicline can be increased when it is combined with Rosoxacin.Approved
Roxatidine acetateThe serum concentration of Varenicline can be increased when it is combined with Roxatidine acetate.Approved
SotalolThe risk or severity of adverse effects can be increased when Sotalol is combined with Varenicline.Approved
SparfloxacinThe serum concentration of Varenicline can be increased when it is combined with Sparfloxacin.Approved
TacrineThe risk or severity of adverse effects can be increased when Tacrine is combined with Varenicline.Withdrawn
TemafloxacinThe serum concentration of Varenicline can be increased when it is combined with Temafloxacin.Withdrawn
TimololThe risk or severity of adverse effects can be increased when Timolol is combined with Varenicline.Approved
TrimethoprimThe serum concentration of Varenicline can be increased when it is combined with Trimethoprim.Approved, Vet Approved
TrovafloxacinThe serum concentration of Varenicline can be increased when it is combined with Trovafloxacin.Approved, Withdrawn
TubocurarineThe risk or severity of adverse effects can be increased when Tubocurarine is combined with Varenicline.Approved
Food InteractionsNot Available
References
Synthesis Reference

Vinod Kumar Kansal, Suhail Ahmad, Amit Gupta, “PROCESSES FOR THE PREPARATION OF VARENICLINE AND INTERMEDIATES THEREOF.” U.S. Patent US20090318695, issued December 24, 2009.

US20090318695
General References
  1. Jorenby DE, Hays JT, Rigotti NA, Azoulay S, Watsky EJ, Williams KE, Billing CB, Gong J, Reeves KR: Efficacy of varenicline, an alpha4beta2 nicotinic acetylcholine receptor partial agonist, vs placebo or sustained-release bupropion for smoking cessation: a randomized controlled trial. JAMA. 2006 Jul 5;296(1):56-63. [PubMed:16820547 ]
  2. Mihalak KB, Carroll FI, Luetje CW: Varenicline is a partial agonist at alpha4beta2 and a full agonist at alpha7 neuronal nicotinic receptors. Mol Pharmacol. 2006 Sep;70(3):801-5. Epub 2006 Jun 9. [PubMed:16766716 ]
  3. Obach RS, Reed-Hagen AE, Krueger SS, Obach BJ, O'Connell TN, Zandi KS, Miller S, Coe JW: Metabolism and disposition of varenicline, a selective alpha4beta2 acetylcholine receptor partial agonist, in vivo and in vitro. Drug Metab Dispos. 2006 Jan;34(1):121-30. Epub 2005 Oct 12. [PubMed:16221753 ]
  4. Coe JW, Brooks PR, Vetelino MG, Wirtz MC, Arnold EP, Huang J, Sands SB, Davis TI, Lebel LA, Fox CB, Shrikhande A, Heym JH, Schaeffer E, Rollema H, Lu Y, Mansbach RS, Chambers LK, Rovetti CC, Schulz DW, Tingley FD 3rd, O'Neill BT: Varenicline: an alpha4beta2 nicotinic receptor partial agonist for smoking cessation. J Med Chem. 2005 May 19;48(10):3474-7. [PubMed:15887955 ]
  5. Kuehn BM: FDA speeds smoking cessation drug review. JAMA. 2006 Feb 8;295(6):614. [PubMed:16467225 ]
External Links
ATC CodesN07BA03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (334 KB)
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentAlcohol Use Disorders (AUD) / Smoking, Cigarette1
0TerminatedTreatmentCessation, Smoking1
1CompletedNot AvailableCessation, Smoking1
1CompletedNot AvailableHealthy Volunteers / Non-Smoking1
1CompletedNot AvailableMethamphetamine Abuse / Methamphetamine Dependence / Substance Abuse1
1CompletedBasic ScienceTobacco Use Disorders1
1CompletedTreatmentAdditional, Effective Methods to Stop Smoking1
1CompletedTreatmentAmphetamine Addiction / Crystal Meth Addiction / Methamphetamine Addiction1
1CompletedTreatmentCessation, Smoking2
1CompletedTreatmentOpioid Dependence / Pain, Chronic1
1CompletedTreatmentSmoking1
1Not Yet RecruitingBasic ScienceCognitive Function / Dopamine D2/3 Receptor Availability / Methamphetamine Abuse1
1RecruitingTreatmentAlcohol Consumption / Heavy Drinking / Nicotine Dependence / Smoking, Cigarette1
1WithdrawnNot AvailableMethamphetamine Abuse / Methamphetamine Dependence / Substance Abuse1
1WithdrawnOtherDrug Addiction1
1, 2CompletedTreatmentAlcohol Drinking1
1, 2CompletedTreatmentLung Cancers1
1, 2CompletedTreatmentNicotine Dependence / Smoking1
1, 2CompletedTreatmentTobacco Use Disorders / Weight gain therapy1
1, 2Not Yet RecruitingTreatmentAlcohol Use Disorder (AUD)1
1, 2WithdrawnNot AvailableNicotine Dependence1
2Active Not RecruitingTreatmentAlcohol Drinking1
2Active Not RecruitingTreatmentSmoking Lapse Behavior1
2CompletedNot AvailableSchizophrenia1
2CompletedTreatmentAlcohol Abuse / Alcohol Drinking / Alcoholism / Smoking1
2CompletedTreatmentAlcohol Dependence1
2CompletedTreatmentAlcohol Dependence / Dependence, Cocaine1
2CompletedTreatmentAlcohol Reactivity1
2CompletedTreatmentAlcoholism2
2CompletedTreatmentAlzheimer's Disease (AD)1
2CompletedTreatmentCessation, Smoking6
2CompletedTreatmentCessation, Smoking / Schizophrenia1
2CompletedTreatmentDependence, Cocaine1
2CompletedTreatmentHeavy Drinking / Nicotine Dependence / Smoking1
2CompletedTreatmentMethamphetamine Abuse / Methamphetamine Dependence / Substance Abuse2
2CompletedTreatmentNicotine Dependence3
2CompletedTreatmentNicotine Dependence / Post-Traumatic Stress Disorder (PTSD) / Smoking, Cigarette / Tobacco Use Disorders1
2CompletedTreatmentNicotine Dependence / Tobacco Use Cessation / Tobacco Use Disorders1
2CompletedTreatmentSchizoaffective Disorders / Schizophrenia1
2CompletedTreatmentSchizophrenia / Smoking, Cigarette1
2CompletedTreatmentSmoking2
2CompletedTreatmentSmoking Behavior / Smoking Lapse Behavior / Smoking Relapse Behavior1
2CompletedTreatmentSmoking, Cigarette2
2CompletedTreatmentSpinocerebellar Ataxia Type 31
2CompletedTreatmentTobacco Dependence1
2CompletedTreatmentTobacco Use Disorders1
2Enrolling by InvitationTreatmentParkinson's Disease (PD)1
2Not Yet RecruitingTreatmentNicotine Dependence1
2RecruitingTreatmentAlcohol Use Disorder (AUD) / Nicotine Dependence1
2RecruitingTreatmentBMI >30 kg/m2 / Smoking, Cigarette1
2RecruitingTreatmentDependence, Cocaine1
2RecruitingTreatmentSubstance Use Disorder (SUD)1
2Unknown StatusTreatmentAlcohol Dependence1
2Unknown StatusTreatmentAlzheimer Disease1
2Unknown StatusTreatmentParkinson's Disease (PD)1
2Unknown StatusTreatmentSmoking1
2WithdrawnBasic ScienceVarenicline and the Blunting of Cocaine Cues1
2WithdrawnTreatmentCessation, Smoking1
2WithdrawnTreatmentDependence, Cocaine1
2WithdrawnTreatmentSchizophrenia1
2, 3Active Not RecruitingPreventionCessation, Smoking / Habits / Smoking1
2, 3Active Not RecruitingTreatmentCessation, Smoking / Tobacco Use Disorders1
2, 3CompletedPreventionTobacco Use Disorders1
2, 3CompletedTreatmentAlcohol Dependence / Smoking / Tobacco Dependence1
2, 3CompletedTreatmentNicotine Dependence / Nicotine Withdrawal1
2, 3CompletedTreatmentSmoking1
2, 3CompletedTreatmentTobacco Abstinence1
2, 3Not Yet RecruitingTreatmentAlcohol Use / Human Immunodeficiency Virus (HIV) Infections / Smoking1
2, 3RecruitingTreatmentBMI >30 kg/m2 / Cessation, Smoking1
2, 3RecruitingTreatmentCessation, Smoking / Opioid Related Disorders1
2, 3TerminatedTreatmentFriedreich's Ataxia1
2, 3TerminatedTreatmentNicotine Dependence / Smoking, Cigarette1
2, 3Unknown StatusTreatmentTobacco Dependence1
3Active Not RecruitingTreatmentCessation, Smoking1
3Active Not RecruitingTreatmentCessation, Smoking / HIV Disease1
3Active Not RecruitingTreatmentNicotine Dependence1
3Active Not RecruitingTreatmentNicotine Dependence / Tobacco Use1
3CompletedNot AvailableCessation, Smoking1
3CompletedPreventionAcute Coronary Syndromes (ACS)1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / COPD Exacerbation / Smoking1
3CompletedTreatmentCessation, Smoking10
3CompletedTreatmentCessation, Smoking / Tobacco Dependence3
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tobacco Dependence1
3CompletedTreatmentNicotine Addiction1
3CompletedTreatmentNicotine Dependence2
3CompletedTreatmentSchizophrenia1
3Not Yet RecruitingPreventionCessation, Smoking / Chronic Obstructive Pulmonary Disease (COPD)1
3Not Yet RecruitingTreatmentCessation, Smoking1
3Not Yet RecruitingTreatmentHIV Disease / Smoking1
3Not Yet RecruitingTreatmentLung Carcinoma1
3RecruitingPreventionSmokers With Cancer1
3RecruitingTreatmentNicotine Dependence3
3TerminatedTreatmentAlcoholism / Nicotine Dependence1
4Active Not RecruitingTreatmentCessation, Smoking / Nicotine Dependence / Smoking1
4Active Not RecruitingTreatmentParkinson's Disease (PD)1
4Active Not RecruitingTreatmentSmoking1
4CompletedNot AvailableCessation, Smoking3
4CompletedDiagnosticCessation, Smoking / Recurrences / Substance-Related Disorders1
4CompletedHealth Services ResearchCessation, Smoking1
4CompletedOtherCraving / Schizophrenia / Smoking1
4CompletedPreventionCerebrovascular Disorders / Cessation, Smoking1
4CompletedPreventionCessation, Smoking / Psychiatric Illness1
4CompletedPreventionCoronary Heart Disease (CHD)1
4CompletedScreeningNicotine Dependence1
4CompletedTreatmentAlcohol Abuse / Cessation, Smoking1
4CompletedTreatmentAsthma1
4CompletedTreatmentAsthma / Community Acquired Pneumonia (CAP) / Pulmonary Disease, Chronic Obstructive1
4CompletedTreatmentBipolar Disorder (BD) / Cessation, Smoking1
4CompletedTreatmentBipolar Disorder (BD) / Schizoaffective Disorders / Schizophrenia / Smoking1
4CompletedTreatmentCessation, Smoking8
4CompletedTreatmentCessation, Smoking / Depression1
4CompletedTreatmentCessation, Smoking / Smoking / Tobacco Use Disorders1
4CompletedTreatmentNicotine Dependance / Schizophrenia / Tobocco Use Disorder1
4CompletedTreatmentNicotine Dependence1
4CompletedTreatmentSmoking2
4CompletedTreatmentSmoking Addiction1
4CompletedTreatmentTobacco Use Cessation1
4Enrolling by InvitationTreatmentMethadone Maintenance / Smoking, Cigarette1
4Not Yet RecruitingTreatmentAlcohol Consumption / Smoking, Cigarette1
4Not Yet RecruitingTreatmentAlcohol Drinking / Cessation, Smoking1
4Not Yet RecruitingTreatmentCessation, Smoking1
4RecruitingPreventionTobacco Use Cessation1
4RecruitingTreatmentCessation, Smoking4
4RecruitingTreatmentMajor Depressive Disorder (MDD) / Nicotine Dependence1
4RecruitingTreatmentNicotine Dependence1
4RecruitingTreatmentTobacco Use Cessation1
4TerminatedTreatmentAlcohol Dependence / Nicotine Dependence / Schizoaffective Disorders / Schizophrenia1
4TerminatedTreatmentAttention Deficit/Hyperactivity Disorder / Cessation, Smoking1
4Unknown StatusPreventionCessation, Smoking1
4Unknown StatusTreatmentCessation, Smoking / Substance-Related Disorders1
4Unknown StatusTreatmentHypertensive / Smoking, Cigarette1
4Unknown StatusTreatmentNicotine Dependence1
4Unknown StatusTreatmentSchizoaffective Disorders / Schizophrenia / Schizophreniform Disorder1
4Unknown StatusTreatmentSchizophrenia / Smoking, Cigarette1
4Unknown StatusTreatmentSmoking1
4WithdrawnTreatmentPsychosis / Schizoaffective / Schizophrenia1
4WithdrawnTreatmentTobacco Use Disorders1
Not AvailableActive Not RecruitingNot AvailableAnxiety / Cardiovascular Diseases / Cessation, Smoking / Depression / Myocardial Infarction (MI) / Respiratory Diseases / Respiratory Illness1
Not AvailableActive Not RecruitingHealth Services ResearchNicotine Dependence, Cigarettes1
Not AvailableActive Not RecruitingPreventionCessation, Smoking / Tobacco Dependence1
Not AvailableActive Not RecruitingTreatmentCessation, Smoking / Head and Neck Cancers1
Not AvailableCompletedNot AvailableCessation, Smoking6
Not AvailableCompletedNot AvailableMalformations1
Not AvailableCompletedNot AvailableNicotine Dependence1
Not AvailableCompletedNot AvailableTobacco Dependence1
Not AvailableCompletedBasic ScienceNicotine Dependence1
Not AvailableCompletedBasic ScienceSubstance Dependence1
Not AvailableCompletedDiagnosticNicotine Dependence1
Not AvailableCompletedHealth Services ResearchDependence, Cocaine / Nicotine Dependence1
Not AvailableCompletedPreventionBladder Cancers / Cervical Cancers / Esophageal Cancers / Gastric Cancers / Head and Neck Cancers / Kidney Cancer / Leukemias / Liver Cancer / Lung Cancers / Pancreatic Cancers / Tobacco Use Disorders1
Not AvailableCompletedPreventionTobacco Use Disorders1
Not AvailableCompletedPreventionUnspecified Adult Solid Tumor, Protocol Specific1
Not AvailableCompletedSupportive CareSmoking1
Not AvailableCompletedTreatmentAlcohol Dependence / Tobacco Dependence1
Not AvailableCompletedTreatmentBipolar Disorder (BD) / Depression / Smoking1
Not AvailableCompletedTreatmentCessation, Smoking1
Not AvailableCompletedTreatmentCessation, Smoking / Diabetes1
Not AvailableCompletedTreatmentCessation, Smoking / Medication Adherence1
Not AvailableCompletedTreatmentCognition in Schizophrenia1
Not AvailableCompletedTreatmentDepressive Disorders / Smoking1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Smoking1
Not AvailableCompletedTreatmentNicotine Dependence3
Not AvailableCompletedTreatmentNicotine Dependence / Tobacco Use Disorders1
Not AvailableCompletedTreatmentPeriodontitis1
Not AvailableCompletedTreatmentSmokers1
Not AvailableCompletedTreatmentTobacco Use Cessation1
Not AvailableCompletedTreatmentTobacco Use Disorders1
Not AvailableEnrolling by InvitationNot AvailableCessation, Smoking1
Not AvailableNot Yet RecruitingHealth Services ResearchAsthma / Chronic Obstructive Pulmonary Disease (COPD) / Smoking1
Not AvailableNot Yet RecruitingOtherNicotine Dependence1
Not AvailableNot Yet RecruitingTreatmentAcute Coronary Syndromes (ACS) / Cessation, Smoking1
Not AvailableNot Yet RecruitingTreatmentNicotine Dependence / Smokeless Tobacco1
Not AvailableRecruitingBasic ScienceSmoking, Cigarette1
Not AvailableRecruitingPreventionCurrent Smokers / Head and Neck Squamous Cell Carcinoma (HNSCC) / Hypopharyngeal Squamous Cell Carcinoma / Laryngeal Squamous Cell Carcinoma / Nasopharyngeal Carcinoma / Oral Cavity Squamous Cell Carcinoma / Oropharyngeal Squamous Cell Carcinoma1
Not AvailableRecruitingTreatmentCoronary Artery Disease1
Not AvailableTerminatedNot AvailableCancer, Breast / Tobacco Dependence1
Not AvailableTerminatedBasic ScienceSmoking1
Not AvailableUnknown StatusTreatmentCessation, Smoking / Nicotine Dependence1
Not AvailableWithdrawnTreatmentDepressive Disorders / Smoking1
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Kit; tabletOral
TabletOral0.5 mg
TabletOral1.0 mg
Tablet, film coatedOral0.5 mg
Tablet, film coatedOral1 mg
Tablet, film coatedOral1.0 mg
Kit
Tablet, film coatedOral.5 mg/1
Tablet, film coatedOral1 mg/1
Prices
Unit descriptionCostUnit
Chantix Continuing Month Pak 56 1 mg tablet Disp Pack148.5USD disp
Chantix Starting Month Pak 0.5 mg X 11, 1 mg X 42 Disp Pack148.5USD disp
Chantix 1 mg tablet2.61USD tablet
Chantix 0.5 mg tablet2.56USD tablet
Chantix 1 mg cont month pak2.56USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2316921 No2004-12-072018-11-13Canada
CA2525874 No2007-11-272024-05-07Canada
US6410550 No2000-05-102020-05-10Us
US6890927 No2002-05-062022-05-06Us
US7265119 No2002-08-032022-08-03Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP0.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0877 mg/mLALOGPS
logP1.39ALOGPS
logP1.01ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)9.73ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.81 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity61.3 m3·mol-1ChemAxon
Polarizability23.12 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9969
Blood Brain Barrier+0.9908
Caco-2 permeable-0.5233
P-glycoprotein substrateSubstrate0.5458
P-glycoprotein inhibitor INon-inhibitor0.7453
P-glycoprotein inhibitor IINon-inhibitor0.9637
Renal organic cation transporterInhibitor0.5489
CYP450 2C9 substrateNon-substrate0.8933
CYP450 2D6 substrateNon-substrate0.6522
CYP450 3A4 substrateNon-substrate0.7428
CYP450 1A2 substrateNon-inhibitor0.507
CYP450 2C9 inhibitorNon-inhibitor0.881
CYP450 2D6 inhibitorInhibitor0.6251
CYP450 2C19 inhibitorNon-inhibitor0.8029
CYP450 3A4 inhibitorNon-inhibitor0.6589
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5453
Ames testNon AMES toxic0.7128
CarcinogenicityNon-carcinogens0.9592
BiodegradationNot ready biodegradable0.9906
Rat acute toxicity2.5914 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9382
hERG inhibition (predictor II)Inhibitor0.5497
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzazepines
Direct ParentBenzazepines
Alternative Parents
Substituents
  • Benzazepine
  • Diazanaphthalene
  • Quinoxaline
  • Indane
  • Azepine
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Pyrazine
  • Heteroaromatic compound
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
partial agonist
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodium ions.
Gene Name:
CHRNA4
Uniprot ID:
P43681
Molecular Weight:
69956.47 Da
References
  1. Nakamura M, Oshima A, Fujimoto Y, Maruyama N, Ishibashi T, Reeves KR: Efficacy and tolerability of varenicline, an alpha4beta2 nicotinic acetylcholine receptor partial agonist, in a 12-week, randomized, placebo-controlled, dose-response study with 40-week follow-up for smoking cessation in Japanese smokers. Clin Ther. 2007 Jun;29(6):1040-56. [PubMed:17692720 ]
  2. McColl SL, Burstein AH, Reeves KR, Billing CB Jr, Stolar M, Sellers EM: Human abuse liability of the smoking cessation drug varenicline in smokers and nonsmokers. Clin Pharmacol Ther. 2008 Apr;83(4):607-14. doi: 10.1038/sj.clpt.6100510. Epub 2008 Feb 20. [PubMed:18288085 ]
  3. Rollema H, Coe JW, Chambers LK, Hurst RS, Stahl SM, Williams KE: Rationale, pharmacology and clinical efficacy of partial agonists of alpha4beta2 nACh receptors for smoking cessation. Trends Pharmacol Sci. 2007 Jul;28(7):316-25. Epub 2007 Jun 18. [PubMed:17573127 ]
  4. Steensland P, Simms JA, Holgate J, Richards JK, Bartlett SE: Varenicline, an alpha4beta2 nicotinic acetylcholine receptor partial agonist, selectively decreases ethanol consumption and seeking. Proc Natl Acad Sci U S A. 2007 Jul 24;104(30):12518-23. Epub 2007 Jul 11. [PubMed:17626178 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Toxic substance binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is blocked by alpha-bungarotoxin.
Gene Name:
CHRNA7
Uniprot ID:
P36544
Molecular Weight:
56448.925 Da
References
  1. Mihalak KB, Carroll FI, Luetje CW: Varenicline is a partial agonist at alpha4beta2 and a full agonist at alpha7 neuronal nicotinic receptors. Mol Pharmacol. 2006 Sep;70(3):801-5. Epub 2006 Jun 9. [PubMed:16766716 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
partial agonist
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA3
Uniprot ID:
P32297
Molecular Weight:
57479.54 Da
References
  1. Mihalak KB, Carroll FI, Luetje CW: Varenicline is a partial agonist at alpha4beta2 and a full agonist at alpha7 neuronal nicotinic receptors. Mol Pharmacol. 2006 Sep;70(3):801-5. Epub 2006 Jun 9. [PubMed:16766716 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
partial agonist
General Function:
Acetylcholine-activated cation-selective channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA6
Uniprot ID:
Q15825
Molecular Weight:
56897.745 Da
References
  1. Mihalak KB, Carroll FI, Luetje CW: Varenicline is a partial agonist at alpha4beta2 and a full agonist at alpha7 neuronal nicotinic receptors. Mol Pharmacol. 2006 Sep;70(3):801-5. Epub 2006 Jun 9. [PubMed:16766716 ]
Drug created on May 16, 2007 14:24 / Updated on May 25, 2017 04:08